Cycling holiday villas and apartments Isle of Wight

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  • Bembridge (20)
  • Bemridge Harbour (1)
  • Bonchurch (7)
  • Brading (4)
  • Brighstone (5)
  • Brook (2)
  • Calbourne (5)
  • Cowes (48)
  • East Cowes (4)
  • Freshwater (24)
  • Godshill (5)
  • Gurnard (13)
  • Knighton, Isle of Wight (1)
  • Lake (1)
  • Nettlestone (1)
  • Newport (7)
  • Newtown (1)
  • Niton (6)
  • Porchfield (3)
  • Rookley (1)
  • Ryde (20)
  • Sandown (41)
  • Seaview (10)
  • Shanklin (36)
  • Shorwell (5)
  • St Helens (3)
  • Totland Bay (5)
  • Ventnor (54)
  • Wellow (2)
  • Whippingham (6)
  • Whitwell (5)
  • Wootton Bridge (9)
  • Wroxall (6)
  • Yarmouth (18)

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379 Holiday homes

Filters applied: Cycling holidays (379)

Travellers going to Isle of Wight are booking November dates now. Secure your holiday home today and have the perfect trip.

(18) Excellent 

24

Isle Of Wight Caravan Hire - Bembridge caravan/mobile home sleeps 8

Isle of Wight / Bembridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
*We have more statics available, so please contact us even if the calendar says unavailable*This fantastic spacious and homely static caravan is in the same area as The Other Statics we have available at Sandhills Holiday Park so if you wanted two or more families to co  …see more

from £100 / night

£350 - £650 / week

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from £100 / night

(12) Excellent 

13

Sea Whispers - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
This is a beautiful chalet which has had excellent reviews over the past few seasons. Recently decorated, the chalet offers plenty of space to accommodate four guests. There is a double bed and bunk beds. The double room has a TV with Freeview and DVD . The chalet fu  …see more

from £35 / night

£240 - £485 / week

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from £35 / night

(4) Very Good 

16

Isle of wight Sandown Chalet 79 - Yaverland chalet sleeps 6

Sandown / Yaverland

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Situated on the coastal path, literally steps from the national trust walkway to Culver Down. So after a stroll with spectacular sea and rural views you will find a great family pub. Location ideal for walking or cycling with many local island attractions. Great for f  …see more

from £29 / night

£200 - £300 / week

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from £29 / night

(7) Very Good 

35

Stable Cottage by OceanBlue - Bonchurch cottage sleeps 8

Isle of Wight / Bonchurch

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Stable Cottage is located at the end of a quiet private lane to the east of the timeless village of Bonchurch. The cottage is a perfect retreat for a family holiday with Monks Bay a two minutes wander down the coastal path. The cottage was renovated in 2013. Through c  …see more

from £10 / night

£1090 - £1990 / week

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from £10 / night

(5) Excellent 

16

Woodland Cottage, Fort Victoria - Yarmouth villa sleeps 8

Isle of Wight / Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
Woodlands Cottage is a stunning four bedroom property overlooking the sea and set in well over an acre of it's own private woodland on the west coast of the Isle of Wight. The property is incredibly tranquil and secluded. The master bedroom has a very spacious wooden d  …see more

from £140 / night

£725 - £2240 / week

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from £140 / night

(82) Excellent 

25

Camellia Cottage - Niton Undercliff cottage sleeps 8

Ventnor / Niton Undercliff

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Child friendly
Four Star - Gold Award - Character accommodation, easily sleeping eight guests. Perfect for the extended family, or two families wishing to share. A real home from home, offering everything you could want. With a traditional welcoming pub a 5 minute walk away it is a pe  …see more

from £120 / night

£570 - £1475 / week

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from £120 / night

(17) Very Good 

7

The Beach Retreat Eco Friendly - Gurnard log cabin sleeps 4

Isle of Wight / Gurnard

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Time to take a breather,,,,in our quirky little gem of a place, get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view, you may want to spend time with your children on the beach, go fishing ( i  …see more

from £60 / night

£420 - £550 / week

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from £60 / night

(14) Very Good 

24

Cedar Croft - Cowes log cabin sleeps 5

Isle of Wight / Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
Take a peaceful break away from the crowds in our quirky little cabin. Get up have a stroll along the beach, on our private bay, then sit outside and have breakfast while looking at the beautiful view and watching the boats sail by, you may want to spend time with your  …see more

from £57 / night

£400 - £670 / week

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from £57 / night

(19) Very Good 

20

Seaspray Chalet - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Child friendly
Seaspray Chalet is fully self catering with an open plan Kitchen and lounge. It provides comfortable accommodation with two bedrooms, one double and one with bunk beds. The Bathroom has a full size bath and shower above. There is plenty of hot water and Electricity and  …see more

from £35 / night

£195 - £490 / week

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from £35 / night

(3) Excellent 

27

Spacious Self-Catering 4 Bedroom Holiday Cottage - Shorwell house sleeps 7

Isle of Wight / Shorwell

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 3 km
  • Child friendly
  • Private garden
A rural village holiday getaway close to the unspoilt south west cost of the Isle of Wight. New for 2015 Church View is a stylish and modern family house set in the picturesque village of Shorwell opposite its historic church and country pub. Surrounded by beautiful cou  …see more

from £100 / night

£600 - £1350 / week

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from £100 / night

(10) Excellent 

20

Wight Cottage, Fort Victoria - Fort Victoria cottage sleeps 4

Yarmouth / Fort Victoria

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Wight Cottage is adjacent to Fort Victoria and close to the pretty harbour town of Yarmouth. The cottage has wonderful sea views from the master bedroom and from the living room, plus plenty of outside space for safe playing, barbequing with family/friends, or simply en  …see more

from £85 / night

£595 - £1245 / week

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from £85 / night

(12) Excellent 

18

Carlton Cottage - West Cowes cottage sleeps 7

Cowes / West Cowes

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.08 km
  • Child friendly
This is a newly built, absolute gem of a cottage which is set just back from the waterfront with some Solent views. A delightful detached property fitted to the highest quality and standards. Comfortably sleeps up to 7 people in flexible accommodation to suit single or  …see more

from £180 / night

£740 - £2600 / week

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from £180 / night

11

Charnwood Cottage - Brading cottage sleeps 4

Isle of Wight / Brading

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Fri 22 Jul 2016 - Fri 29 Jul 2016 SPECIAL OFFER NOW ONLY £400 ** FERRY TRAVEL INCLUDED ** Mon 25 Jul 2016 - Fri 29 Jul 2016 4 NIGHT SPECIAL OFFER NOW ONLY £275 ** DISCOUNTED FERRY TRAVEL** The cottage is ideally located for parties wishing to explore all that the  …see more

from £104 / night

£345 - £625 / week

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from £104 / night

(20) Excellent 

16

SEAVIEW HOLIDAY CHALET - Yaverland chalet sleeps 4

Sandown / Yaverland

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
The chalet is modern and well equipped for a family of 4, it has sea views from the front and side windows, and over looks the beautiful cliffs of Culver down.It is situated on the edge of national trust land which is accessible from the site with many miles of walks ac  …see more

from £25 / night

£175 - £550 / week

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from £25 / night

(12) Excellent 

19

Stickey Wicket - Niton chalet sleeps 2

Isle of Wight / Niton

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 5 km
  • Car not necessary
Sticky Wicket is a cosy one bedroom chalet set among beautiful gardens in the charming village of Niton near Ventnor. The property has one bedroom with an en-suite shower room, kitchen and lounge with sofa and tv. Situated in a row of similar south facing properties it  …see more

from £40 / night

£240 - £425 / week

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from £40 / night

(6) Excellent 

26

2 The Granary, Brighstone - Brighstone cottage sleeps 4

Isle of Wight / Brighstone

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
Charming Grade II listed character cottage, quietly situated on the edge of the pretty village of Brighstone, 1/2 mile from the sea. 2 The Granary originally formed part of Brighstone Mill and dates back to 1700. Converted in 1990, the living room is on the first floor  …see more

from £99 / night

£375 - £785 / week

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from £99 / night

22

Yangeyange#65 - Seaview chalet sleeps 4

Isle of Wight / Seaview

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Child friendly
(Preferential ferry prices for our guests: please ask for details) Our three Salterns Beach Chalets in this small development have been modernised to Premier standard to provide most comfortable accommodation for your seaside holiday. They are superbly situated with Ya  …see more

from £58 / night

£249 - £425 / week

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from £58 / night

(22) Excellent 

12

LONGSHOREMANS COTTAGE - Sandown cottage sleeps 4

Isle of Wight / Sandown

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Longshoremans Cottage is located close to all the amenities Sandown has to offer and benefits from off road parking. It was originally converted from a boat house, whose owners earnt their living from working on the beach. The cottage is fully equipped with all the esse  …see more

from £40 / night

£235 - £420 / week

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from £40 / night

(4) Excellent 

12

Blue Gables - Bembridge Village bungalow sleeps 6

Bembridge / Bembridge Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
This spacious detached bungalow is in a quiet residential area of the village of Bembridge. It is within walking distance of Forelands Beach and the Crab and Lobster Inn and beach café. Blue Gable is close to the Lifeboat Station, local shops and village centre with ea  …see more

from £85 / night

£595 - £950 / week

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from £85 / night

(10) Excellent 

16

Number 58 Brambles Chine - Freshwater bungalow sleeps 5

Isle of Wight / Freshwater

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
Number 58 is a perfect holiday getaway on the beautiful Isle of Wight. Sleeping up to five people, this two bedroom self-catering semi-detached bungalow based at Brambles Chine, West Wight is just minutes from the ferry terminal in nearby Yarmouth and only yards from th  …see more

from £70 / night

£390 - £520 / week

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from £70 / night

(7) Very Good 

35

Aisla Cottage - East Cowes house sleeps 5

Isle of Wight / East Cowes

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary
Sleeps 4 people comfortably but with capacity for up to 5. 2 bedroom sea-front cottage in East Cowes with incredible sea and River Medina views. Now with BT Infinity Superfast Broadband. The cottage is within easy walking distance of the Red Funnel Ferry and near to the  …see more

from £125 / night

£575 - £1375 / week

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from £125 / night

(1) Excellent 

12

Ledge View - Bembridge Village house sleeps 6

Bembridge / Bembridge Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
Ledge View is a stunning home yards from the popular Forelands Beach in Bembridge, sleeping up to 8 people. The house has been recently upgraded and furnished to a very high standard throughout and also has plenty of parking space. The traditional and friendly Crab and  …see more

from £100 / night

£595 - £1295 / week

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from £100 / night

(3) Very Good 

12

1 Driftwood - Bembridge Harbour apartment sleeps 4

Bembridge / Bembridge Harbour

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
1 Driftwood is a delightful and bright first floor apartment set in a unique location enjoying panoramic views of The Solent and is adjacent to the beach and coastal walks. Bembridge Ledge is accessed across the grassland in front of the property or via Fishermans Walk.  …see more

from £50 / night

£230 - £350 / week

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from £50 / night

(23) Excellent 

23

sea views close to town, safe garden pets welcome - Ventnor house sleeps 7

Isle of Wight / Ventnor

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
This 3 double bedroom house has excellent town sea and downs views and sleeps 7 people [ plus sofa bed]. The accommodation comprises of 3 double bedrooms [ 1 double bed, 2 single, 3 single beds], a bathroom with separate shower, kitchen, lounge and conservatory that l  …see more

from £175 / night

£500 / week

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from £175 / night

(5) Excellent 

23

Smugglers - Ventnor cottage sleeps 7

Isle of Wight / Ventnor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Ask about pets
OPEN ALL YEAR Smugglers is a pretty and cosy early Victorian Cottage in the centre of Ventnor, sleeping 7 people comfortably, plus a cot if required. There is a large double bedroom with a single room attached and a double room with a twin room attached. Both doubles ha  …see more

from £95 / night

£525 - £995 / week

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from £95 / night

(11) Excellent 

32

Seaside Holiday Cottage, Seaview Isle of Wight - Seaview house sleeps 7

Isle of Wight / Seaview

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Private garden
The Lobster Pot is a wonderful, newly renovated family friendly chalet cottage with sea views, in Seaview. Just a short walk to several renowned and award winning beaches such as Priory Bay, Seagrove Bay, Seaview Beach, The Duver and Bembridge Beach. The beaches are pre  …see more

from £85 / night

£799 - £999 / week

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from £85 / night

(18) Excellent 

22

The Coach House, Woodlands Val - Appley cottage sleeps 4

Ryde / Appley

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly
This Grade II listed Coach House is set in tranquil parkland grounds between the resort town of Ryde and Seaview, with views over open fields and woodland, the cottage enjoys a rural atmosphere whilst being within ten minutes walk of the beach. This charming cottage off  …see more

from £85 / night

£595 - £950 / week

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from £85 / night

(2) Excellent 

10

Red squirrels Grange Farm - Wootton Bridge lodge sleeps 6

Isle of Wight / Wootton Bridge

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Ask about pets
  • Private garden
This is a barrier free brand new build. Suitable for wheel chair users. Sleeps 5 to 6. All on one level with car parking and garden. The Lodge comprises of a Large wet room, en-suite double room and two twin rooms, Large kitchen / diner lounge. A veranda to the front  …see more

from £114 / night

£795 / week

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from £114 / night

(12) Excellent 

15

Waterside - Wootton Bridge bungalow sleeps 6

Isle of Wight / Wootton Bridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
This spacious detached 3 bedroom home is set in a stunning location with spectacular views overlooking Wootton Creek and benefits from its own floating pontoon for boats up to 32 feet allowing access to and from The Solent.The accommodation comprises a spacious lounge w  …see more

from £95 / night

£495 - £995 / week

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from £95 / night

19

Norwood - Brading cottage sleeps 8

Isle of Wight / Brading

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
Lovingly restored by the current owners the accommodation retains many character features yet combines the benefits of modern additions which make Norwood House a perfect base for any holiday.The accommodation offers a cosy sitting room with a feature open fireplace, fl  …see more

from £135 / night

£525 - £750 / week

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from £135 / night

(8) Excellent 

13

Salt Air Cottage - Ventnor cottage sleeps 4

Isle of Wight / Ventnor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
A cosy, three-story seaside bolthole with stunning, secret roof terrace. A former fisherman's flint cottage now fully-modernised just 10-minutes walk from Ventnor's lovely promenade, beach and wide range of first-class restaurants and pubs. Ideal base for walking or cy  …see more

from £75 / night

£475 / week

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from £75 / night

(18) Excellent 

7

1 Barton Lodge - Whippingham lodge sleeps 6

Isle of Wight / Whippingham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 4 km
  • Child friendly
  • Car not necessary
The Victorian lodge house is one of a pair situated within the Barton Estate close to Osborne House which was Queen Victoria's holiday residence of choice. It has been beautifully and lovingly refurbished with your comfort in mind. The house sleeps 6 and offers f  …see more

from £95 / night

£585 - £1025 / week

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from £95 / night

(2) Excellent 

8

Bucks Farm (Poachers Hut) - Shorwell barn sleeps 2

Isle of Wight / Shorwell

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Ask about pets
  • Private garden
A choice of three beautifully and stylishly converted barn cottages set in an idyllic rural location, surrounded by open countryside, an Area of Outstanding Natural Beauty, ideal for walkers and cyclists. Each cottage is tastefully furnished and well equipped for two pe  …see more

from £70 / night

£450 - £550 / week

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from £70 / night

(14) Very Good 

23

Hurst View - Norton - Isle of Wight townhouse sleeps 6

Yarmouth / Norton, Isle of Wight

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Child friendly
Awarded a 4 Star accreditation from VisitEngland Hurst View offers high quality Self Catering holiday accomodation for up to 6 guests in this end of terrace townhouse. Hurst View offers high quality holiday accommodation in the attractive and popular holiday resort of N  …see more

from £54 / night

£378 - £970 / week

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from £54 / night

(1) Very Good 

10

The Furlongs - Brading bungalow sleeps 4

Isle of Wight / Brading

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
The premises has recently been subject to upgrading works and is ideally located for guests wishing to explore all that the Island has to offer yet only being 10 minutes drive from popular sandy beaches of Yaverland and Sandown. Brading is one of the islands more histor  …see more

from £47 / night

£330 - £550 / week

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from £47 / night

(10) Excellent 

19

The Old Brewhouse - Calbourne cottage sleeps 5

Isle of Wight / Calbourne

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Set in a rural location in the grounds of an 18th century farmhouse with 1.5 acres of land. the Old Brewhouse is a delightful 2 bedroomed converted brewhouse which won a design award following completion. The accommodation comprises a ground floor double bedroom with a  …see more

from £100 / night

£400 - £800 / week

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from £100 / night

(4) Excellent 

20

Sunnywight Holiday Bungalows - Freshwater bungalow sleeps 4

Isle of Wight / Freshwater

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly
Welcome to the Sunnywight Holiday Bungalow. Self Catering 3 Star Accomadation in Colwell Bay, near Freshwater in the Isle of Wight.In a secluded and quiet part of The Isle of Wight, the ever popular holiday destination, and with direct access to the beach, our holiday b  …see more

from £40 / night

£275 - £485 / week

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from £40 / night

(14) Excellent 

20

7 firs court - Sandown house sleeps 5

Isle of Wight / Sandown

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Child friendly
This newly constructed semi-detached house is suitable for couples and small families alike. The property benefits from off road parking for two cars and an enclosed rear garden with a raised decking area. Ideally situated a short stroll from the beach and esplanade  …see more

from £36 / night

£250 - £745 / week

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from £36 / night

(6) Very Good 

23

Pebbles - Niton Undercliff chalet sleeps 2

Ventnor / Niton Undercliff

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
A contemporary hillside chalet in the southernmost tip of the Isle of Wight, set in beautiful gardens, with views over treetops towards the sea, and adjacent to the coastal path. Spend a relaxing week at Pebbles, a thoughtfully equipped compact terraced chalet, tucked a  …see more

from £45 / night

£270 - £405 / week

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from £45 / night

12

1 Windmill Cottages - WILLOW - Bembridge Village cottage sleeps 4

Bembridge / Bembridge Village

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Pet friendly
These delightfull. newly built cottages are set in the heart of Bembridge village. When you walk in to the cottage, you get an immediate feeling that everything has been catered for. The kitchen is fully equipped, the king size bedroom upstairs is wonderfully comfortabl  …see more

from £50 / night

£395 - £695 / week

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from £50 / night

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